A compound having a tin functional group has been known to be converted to various compounds e.g. by Stille reaction (e.g. Non-Patent Documents 1, 2, 3 and 4). Further, it has been known to undergo homocoupling in the presence of a palladium catalyst (e.g. Non-Patent Document 5).
Further, it has been known that in a compound having a vinyltin functional group, the tin functional group is further stereoselectively converted to a halide atom as the case requires (e.g. Non-Patent Documents 6, 7, 8, 20, 21 and 22) and that a vinyl halide compound reacts with various organometric reagents (e.g. Non-Patent Documents 4, 20, 21 and 22).
On the other hand, a compound having a carbamoyl group or a thiocarbamoyl group may undergo, for example, Curtius rearrangement using lead tetraacetate to prepare a compound having an isocyanate group or a isothiocyanate group (e.g. Non-Patent Document 9).
An isocyanate group and an isothiocyanate group can be converted to various substituents utilizing their reactivity. For example, they are useful for preparation of a urea compound or a thiourea compound by reaction with an amine (e.g. Non-Patent Document 10) or of a carbamate compound or a thiocarbamate compound by reaction with an alcohol (e.g. Non-Patent Document 11).
Further, in preparation of an isocyanate compound or a thioisocyanate compound, by subsequent reaction with an amine or an alcohol directly without isolation and purification, a urea compound or a carbamate compound can be prepared (e.g. Non-Patent Document 12).
Further, by reducing a compound having an isocyanate group or an isothiocyanate group, a compound having a formylamino group or a thioformylamino group can be obtained (e.g. Non-Patent Document 13). Such groups can be converted to an isonitrile group by the action of p-tosyl chloride (e.g. Non-Patent Document 14) or phosphorus oxychloride (e.g. Non-Patent Document 15).
Many compounds having an isonitrile group are present naturally and develop various physiological activities (e.g. Non-Patent Document 16). As one example, xanthocillin X analogs may be mentioned. Xanthocillin analogs have been known to have a wide range of antimicrobial action and have been reported to have antiviral action, VEGF and COX-2 inhibitory action (e.g. Patent Document 1), aromatase inhibitory action (e.g. Patent Document 2), antitumor action (e.g. Patent Documents 3 and 4), insecticidal action (e.g. Patent Document 5), etc. in addition. Further, as found by the applicants, they are useful compounds which have been known to have thrombopoietin receptor affinity and agonist activity (e.g. Patent Document 6).
Further, by utilizing an isonitrile group which is a reactive functional group, a group of compounds can be prepared by utilizing Ugi reaction and Passerini reaction (e.g. Non-Patent Documents 17, 18 and 19).
As α-substituted vinyltin compounds having a reactive functional group at the α-position in addition to a tin functional group, the following have been known, but one having a nitrogen functional group or one having a carbamoyl group as its starting material has not yet been known.
1) α-alkylcarbonyl-vinyltin compounds and α-arylcarbonyl-vinyltin compounds (e.g. Non-Patent Document 20).
2) α-silyl-substituted vinyltin compounds and α-alkoxycarbonyl-substituted vinyltin compounds (e.g. Non-Patent Documents 21 and 22).
3) α-alkylaminocarbonyl-substituted vinyltin compounds which are vinyltin compounds having a nitrogen functional group at the α-position, for which patents have been applied by BASF (e.g. Patent Documents 7 and 8).
Non-Patent Document 1: Journal of the American Chemistry Society, 100, p. 3636 (1978).
Non-Patent Document 2: Journal of the American Chemistry Society, 101, p. 4992 (1979).
Non-Patent Document 3: Angewandte Chemie International Edition in English, 25, p. 508 (1997).
Non-Patent Document 4: Organic Reaction, 50, p. 1-652 (1997).
Non-Patent Document 5: Tetrahedron Letters, 42, p. 7729 (2001).
Non-Patent Document 6: Journal of Medicinal Chemistry, Vol. 45, No. 6, p. 1253 (2002).
Non-Patent Document 7: Journal of Medicinal Chemistry, Vol. 46, No. 6, p. 925 (2003).
Non-Patent Document 8: Organic Letters, Vol. 4, No. 20, p. 3391 (2002).
Non-Patent Document 9: Journal of Organic Chemistry, 40, p. 3554 (1975).
Non-Patent Document 10: Chemische Berichte, 81, p. 36 (1948).
Non-Patent Document 11: Synthesis, p. 131 (1989).
Non-Patent Document 12: Journal of Organic Chemistry, 24, p. 3554 (1975).
Non-Patent Document 13: Journal of the American Chemistry Society, 95, p. 1669 (1973).
Non-Patent Document 14: Journal of Organic Chemistry, 23, p. 1221 (1958).
Non-Patent Document 15: Bioscience, Biotechnology, and Biochemistry, 57(4), p. 659 (1993).
Non-Patent Document 16: Angewandte Chemie International Edition in English, 39, p. 3168 (2000).
Non-Patent Document 17: Angewandte Chemie International Edition in English, 39, p. 3168 (2000).
Non-Patent Document 18: Organic Letters, 6, p. 4231 (2004).
Non-Patent Document 19: Molecules, 8, p. 53 (2003). http://www.mdpi.org/
Non-Patent Document 20: TETRAHEDRON, Vol. 49, No. 21, p. 4677 (1993).
Non-Patent Document 21: TETRAHEDRON, Vol. 48, No. 40, p. 8801 (1992).
Non-Patent Document 22: Tetrahedron Letters, Vol. 33, No. 31, p. 4495 (1992).
Patent Document 1: JP-A-2004-115504
Patent Document 2: JP-A-7-69883
Patent Document 3: JP-A-2-304058
Patent Document 4: JP-A-4-182427
Patent Document 5: JP-A-2-40324
Patent Document 6: WO2004/016264
Patent Document 7: WO03/076392
Patent Document 8: WO03/082822